Bay Harbor Islands' Concert in the Park Now Starts in October, and the Market Comes With It

On Saturday, October 24, 95th Street Park will host the first "Bay Harbor Live + Artisan Market." It runs from 5:30 to 8:30 p.m. at 1185 95th Street, with Miami vocalist LeNard Rutledge as the headliner. The name is new. The bigger change is the Town's calendar. Over the past two years, the park concert and the evening market appeared as separate listings, usually on spring Sundays. They now appear as one listing that starts earlier, falls mostly on Saturdays, and runs from October to May.

The concert series has existed for years. This season is the first time the Town has scheduled it as a season.

What the Calendar Used to Say

The Town's own event pages show how the format changed. Each row below is copied from a listing for 95th Street Park.

Two things stand out in that record. First, every concert in it fell on a Sunday, and the music started at 7 p.m. Second, the market and the music kept appearing as two separate events. In March 2026, the market ended at 7 p.m., when the concert began. In April 2026, the Town renamed the market "Bay Harbor Night Artisan Market," ran it from 4 to 8 p.m., and overlapped it with a concert from 7 to 8:30 p.m. It still had its own listing.

The two listings also spell the same jazz name two ways: "Jean Cazel" in March and "Jean Caze" in April. The calendar doesn't say whether that is a typo or two different performers. Jean Caze is a jazz trumpeter, composer, and educator. His official biography lists performances with Herbie Hancock, Aretha Franklin, Arturo Sandoval, and Roy Hargrove, and a master's degree from Florida International University.

One Listing, One Evening

The April 2026 overlap previewed the new format. Starting this month, the calendar shows one event with one time slot, "Bay Harbor Live + Artisan Market," from 5:30 to 8:30 p.m. The market no longer opens hours before the band, and the music no longer starts as the market packs up. Both run for the same three hours.

The new slot starts 90 minutes earlier than the 7 p.m. concerts of 2025 and early 2026, and ends 30 minutes earlier than those 9 p.m. finishes. On a Saturday, that puts the evening in the early dinner hour and leaves the rest of the night open.

A Season That Starts in October

The second change is the schedule. The Town's calendar pages for October, November, and December 2025 show no concert or market listings at the park, and the earlier listings in the table cluster between February and May. A few older months could not be loaded, so the record is incomplete. Still, every concert in the table falls between February and May. The 2026–27 schedule, as currently posted, begins in October:

1. Saturday, October 24, 2026: LeNard Rutledge
2. Saturday, November 14, 2026: Flamenco Roots
3. Saturday, December 12, 2026: The Motowners
4. Saturday, February 20, 2027: Gafieira Rio Miami + Samba 305
5. Sunday, March 14, 2027: Juke
6. Saturday, May 8, 2027: Cortadito Trio

All six editions are listed for 5:30 to 8:30 p.m. at 95th Street Park. The January and April 2027 calendar pages had no Bay Harbor Live listing when checked, so the posted season currently skips those months. That could change as the Town adds events. March 14 is the only Sunday date. Every other edition is on a Saturday.

That makes six town nights across eight months, roughly one a month. Last season's park concerts were packed into early spring.

Who Is on the Bill

The lineup moves from jazz vocals to flamenco, Motown, Brazilian big band, blues, and Cuban son. Here is what each act's own materials and the local press say about them.

LeNard Rutledge opens the season on October 24. He grew up in Miami, and his influences include jazz, hymns, funk, and classical music. He was the featured vocalist with the Melton Mustafa Orchestra until 2003. In May 2006, Miami New Times named him Best Jazz Artist, the same year he released his first CD, Hello World.

Flamenco Roots plays November 14. The Town's listing gives only the act's name, and no profile of a Miami group by that name turned up in published sources. The calendar listing is the only reliable information on this booking for now.

The Motowners close the fall run on December 12. The group bills itself as a Motown tribute band, with a repertoire that includes the Temptations and the Four Tops. Its official site says it can be booked in lineups of four to 13 performers.

Gafieira Rio Miami shares the February 20 date with Samba 305. Gafieira Rio Miami describes itself as an 11-piece Brazilian big band that mixes samba, jazz, soul, and funk. Latin GRAMMY-winning bassist Diogo Brown founded the band in 2020 and leads it, with musicians from Brazil, Venezuela, and the United States. It has played Pinecrest Gardens, Arts Garage, Faena Theater, and Lincoln Center. No group called Samba 305 could be confirmed in published sources, so the Town's listing is the only reference for that act.

Juke plays on Sunday, March 14, and has played this park before. The Town's May 19, 2024 Concert In The Park listing called Juke "a blues band with a powerful engine and a bottomless soul," led by frontman and harmonica player Eric Garcia. In July 2025, Miami New Times described Garcia as a third-generation Miamian whose band draws on gospel, blues, and improvisation. It also noted past stages including Tobacco Road and the Fillmore, and Garcia's "Best Songwriter" title in the paper's 2023 Best of Miami issue.

Cortadito closes the season on May 8, listed by the Town as Cortadito Trio. The group's artist page describes a Miami-based collective that plays traditional Cuban folk and acoustic son. Jose Elias founded it in 2011 with Julio Cesar Rodriguez Delet, after 12 years in the Grammy-nominated Conjunto Progresso. Miami New Times named Cortadito Best Latin Act in 2019.

Juke is the only act the calendar shows returning from the old format, and it is booked into the new one.

What the Old Listings Asked of Guests

The 2026–27 listings reviewed for this post give the name, time, place, and headliner, but no attendance rules. The most recent written rules found are from the 2024 Juke concert:

"Concerts In The Park are exclusively for Town residents and their guests. Please bring your own blanket or chair and your ID. No glass or Styrofoam containers please and no pets."

Those were the rules for the earlier series. They have not been confirmed for Bay Harbor Live, and adding a market could change how the Town handles entry. The Town's calendar and the Morris N. Broad Community Center at 1175 95th Street are the places to check before October 24.

The Rest of October on 95th Street

The new series lands in a busy month for the park and community center. The Town calendar for October 2026 also lists:

• BINGO Night, Thursday, October 8, 6 to 8 p.m., Meeting Room 1 at 1175 95th Street
• Coffee with a Cop, Tuesday, October 13, 9:30 to 10:30 a.m., at Coffee Break, 1166 Kane Concourse, hosted by the Bay Harbor Islands Police Department
• Senior Trip to the Wiener Museum of Decorative Arts in Hollywood, Wednesday, October 14, leaving the community center at 1 p.m., with transportation provided
• Spooky Parade, Friday, October 30, 3:30 to 4:30 p.m., at 95th Street Park

The Spooky Parade takes place on the same lawn six days after the first Bay Harbor Live. Last fall, the Town's calendar showed no park concert at all. This October, the park has two Town events within a week.

If a Saturday at 95th Street Park is part of why you value island life, and you are thinking about buying on the islands, buying a second home here, or selling a property here, Allen Davoudpour and his team can talk through which buildings and blocks put the park within an easy walk. Schedule a Consultation, and we will take it from there with the discretion you expect.